Propargyl bromide → N-cyano-N-propargyl-3-trifluoromethylaniline

HRID 5319

Reaction equation

HRID 5319 reaction equation
[C:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]#[CH:22]>CC(C)=O>[C:1]([N:3]([CH2:22][C:21]#[CH:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:5]=1)#[N:2]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 110741023-(Trifluoromethyl)phenylcyanamide

Product 1

HCID 22416968N-cyano-N-propargyl-3-trifluoromethylanilineYield 63.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of N-cyano-3-trifluoromethylaniline (5.0 g) in acetone (100 ml), potassium carbonate (7.4 g) and propargyl bromide (3.5 g) were added, and the resultant mixture was stirred at room temperature for 10 hours, followed by filtration of the reaction mixture. The solvent was removed from the filtrate by distillation under reduced pressure, and the residue was subjected to column chromatography to give N-cyano-N-propargyl-3-trifluoromethylaniline (3.8 g). The thus obtained N-cyano-N-propargyl-3-trifluoromethylaniline (1 g) and a catalytic amount of triethylamine were dissolved in methanol (30 ml), and the resultant mixture was cooled to 0° C. Hydrogen sulfide was gradually introduced into the mixture for 20 minutes while keeping the temperature at 0° C., followed by introduction of nitrogen gas to remove hydrogen sulfide. The solvent was removed by distillation, and the residue was subjected to column chromatography to give 0.2 g of 2-imino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine (Compound (ix)).

Workup

  1. filtrationfollowed by filtration of the reaction mixture
  2. customThe solvent was removed from the filtrate by distillation under reduced pressure

Sources & evidence

ORD record
ord-3292278c79b24e9e918e562e44f20d64
Source dataset
uspto-grants-1993_09
Patent number
US05244863

Linked notes

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